CN207913283U - Phenyl bonded silica solid-phase extraction column - Google Patents
Phenyl bonded silica solid-phase extraction column Download PDFInfo
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- CN207913283U CN207913283U CN201721169114.4U CN201721169114U CN207913283U CN 207913283 U CN207913283 U CN 207913283U CN 201721169114 U CN201721169114 U CN 201721169114U CN 207913283 U CN207913283 U CN 207913283U
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- bonded silica
- phenyl bonded
- sieve plate
- phase extraction
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Abstract
The utility model provides a kind of phenyl bonded silica solid-phase extraction column, it is with cavity column tube (1), the cavity column tube (1) is being internally provided with upper sieve plate (2) and lower sieve plate (4), filler (3) is filled between the upper sieve plate (2) and lower sieve plate (4), the filler is phenyl bonded silica.
Description
Technical field
The utility model is related to a kind of novel phenyl bonded silica Solid Phase Extraction for being extracted to chromocor compound
Column belongs to analytical chemistry field.
Background technology
Flavones is a kind of natural polyphenol substance, is widely present in plant tissue, have remove free radical, it is anti-oxidant,
The multiple functions such as antitumor, sterilization, liver protection, strengthen immunity, occupy critical positions in Natural Medicine Chemistry.Daily life
In, it is more with the presence of flavones in health food or drug.The enrichment detecting method for developing Accurate Determining flavones content, for ensuring Huang
Ketone product quality has great importance.
Solid phase extraction techniques as one using solid material as adsorbent, the skill of analyte in extraction and separation liquid sample
Art, has that enrichment times are high, organic solvent consumption is few, simple operation and other advantages, is very suitable for micro analyzed in complex sample
The enrichment and detection of object.The core of solid phase extraction techniques is fiber material, and performance directly determines effect of extracting.In recent years,
With the development of material science, different types of fiber material emerges one after another, such as the organic bone of graphene, ionic liquid, metal
Frame material, the application limited into materials such as materials make solid phase extraction techniques achieve tremendous development.
It is the usual way for preparing Solid Phase Extraction material to be bonded different chemical functional groups in Silica Surface, wherein carbon 18
Bonded silica gel is Solid Phase Extraction material most common and being commercialized.However, 18 bonded silica gel of carbon and analyte it
Between there is only single hydrophobic effects, it is difficult to effectively extraction the stronger flavones molecule of polarity.In the prior art, had non-special
Sharp document 1 has effectively extracted the flavones molecule in aqueous solution, however, institute in this method by preparing nitroindoline bonded silica gel
The nitroindoline bonded silica gel synthetic method used is complex, and fiber material cost is higher.Therefore, for exploitation in this field
Preparation method is simple, it is lower-cost simultaneously, still deposited with the Solid Phase Extraction material of higher chromocor compound extraction efficiency
In actual demand.
Non-patent literature 1：N.Wang, X.J.Liang, Q.Li, Y.Liao and S.J.Shao, Nitro-
Substituted 3,3 '-bis (indolyl) methanemodified silica gel as a sorbent for
Solid-phase extraction of flavonoids.RSC Adv., 2015,5,15500-15506.
Utility model content
To solve the above subject, utility model people is by concentrating on studies and many experiments, it was thus unexpectedly found that by with
Phenyl trichlorosilane is matrix, prepares phenyl bonded silica, and phenyl bonded silica solid phase is made using the phenyl bonded silica
Extraction column, can efficiently extracting flavone compound, and the phenyl bonded silica solid-phase extraction column also has preparation method letter
Single easy, lower-cost advantage, so as to complete the utility model.
In a first aspect, the utility model provides a kind of phenyl bonded silica solid-phase extraction column, with cavity column tube
1, the cavity column tube 1 is being internally provided with upper sieve plate 2 and lower sieve plate 4, is filled between the upper sieve plate 2 and lower sieve plate 4
Filler 3, the filler are phenyl bonded silica.
In a preferred embodiment, the grain size of the filler 3 is 50~80 μm, and usage amount is 80~120mg, preferably
100mg；The specific surface area of the filler 3 is ＞ 300m2/g。
In further preferred embodiment, the cavity column tube 1 is glass cavity column tube or polypropylene cavity column tube；
The shape of the cavity column tube 1 is cylinder, volume 6mL；The internal diameter of the cavity column tube 1 is 1-1.5cm, preferably
1.3cm。
In further preferred embodiment, the diameter of the upper sieve plate 2 and the lower sieve plate 4 and the cavity column tube
1 internal diameter is consistent；The upper sieve plate 2 and the lower sieve plate 4 have sieve pore, and the aperture of the sieve pore is 3-10 μm, preferably 5 μ
m；And/or the thickness of the upper sieve plate 2 and the lower sieve plate 4 is 1~2mm.
In second aspect, the utility model provides the preparation method of the phenyl bonded silica solid-phase extraction column, described
Method includes the following steps：
(a) silica gel is placed in nonpolar solvent, phenyl trichlorosilane and catalyst is added, be heated to reflux under stiring straight
It is completed to reaction, then purified processing obtains phenyl bonded silica；
(b) phenyl bonded silica is packed into Solid Phase Extraction column tube, is compacted with sieve plate, the phenyl bonded silica solid phase is made
Extraction column.
In a preferred embodiment, in the step (a), the nonpolar solvent is toluene, and the catalyst is pyrrole
Pyridine.
In further preferred embodiment, being calculated with 100mL toluene, the usage amount of the silica gel is 2.0-4.0g,
It is preferred that 3.0g；The usage amount of the phenyl trichlorosilane is 0.75-1.5mL, preferably 1mL；The additive amount of the pyridine is 0.08-
0.12mL, preferably 0.1mL；Described be heated to reflux carries out 10-15h, preferably 12h；The purification process includes centrifugal treating, successively
With ethyl alcohol and water washing and drying.
In the third aspect, the utility model additionally provides a kind of phenyl bonded silica Solid Phase Extraction using the utility model
The method that column extracts chromocor compound, the described method comprises the following steps：
(1) the phenyl bonded silica solid-phase extraction column of the utility model is eluted and is activated with first alcohol and water；
(2) flavones working solution to be measured is made to pass through phenyl bonded silica solid-phase extraction column by pumping driving；
(3) it is eluted by phenyl bonded silica solid-phase extraction column using methanol, obtains eluent.
In a preferred embodiment, in the step (1), the usage amount of the first alcohol and water is respectively 5mL；The step
Suddenly in (2), the pump is peristaltic pump；The dosage of the flavones working solution to be measured is 20~150mL, preferably 50mL, and prior
It is adjusted to pH value 4~5, the state of preferable ph 4.0；The flavones working solution to be measured passes through the phenyl bonded silica solid phase
The flow velocity of extraction column is 1.5~2.0mL/min, preferably 2.0mL/min；In the step (3), the usage amount of the methanol is
1.0mL, the flow velocity are no more than 0.4mL/min, preferably 0.4mL/min.
On the other hand, the utility model is further related to using high performance liquid chromatography to the chromocor compound in above-mentioned eluent
The method being detected.
In a preferred embodiment, the chromatographic condition of the high performance liquid chromatography is：ODS analytical columns (150mm ×
4.6mm I.D.)；With methanol and H3PO4Aqueous solution [0.2wt%] is that mobile phase A carries out gradient elution with B：0-0.5min is0.51-12.5min is12.51-25min isFlow rate of mobile phase：1.0mL/
min；Column temperature：25℃；Sampling volume：20μL；UV detector, wavelength 360nm.
Compared with prior art, the utility model provides a kind of new phenyl bonded silica solid-phase extraction column, has
Prepare advantage simple and easy to do, of low cost, and can be simple and efficient by the phenyl bonded silica solid-phase extraction column pair
Chromocor compound is extracted, and then can be used for chromatography detection.This method has the wide range of linearity, low detection limit,
It is applicable to the enrichment detection of chromocor compound in a variety of actual samples, therefore before having good performance and wide application
Scape.
Description of the drawings
Fig. 1 shows the structural schematic diagram of the phenyl bonded silica solid-phase extraction column of the utility model.
Fig. 2 shows the scanning electron microscopic picture of phenyl bonded silica prepared by embodiment 2.
Fig. 3 shows the infrared spectrum of phenyl bonded silica and silica matrix.
Fig. 4 A-4C show the pass between the operating parameter of Solid Phase Extraction and the pH value and extraction efficiency of flavones working solution
System.
Fig. 5 A-5C show the relationship between the parameter of elution step and extraction efficiency.
Specific implementation mode
To those skilled in the art it is known that phenyl trichlorosilane is a kind of simple, common silane examination
Agent, utility model people have found for the first time, using the phenyl bonded silica that it is prepared as reactant, theoretically can effectively extract Huang
Ketone compound, this may be the result with π-π interactions between the presence due to phenyl ring, with flavones molecule.
Embodiment
Next, the utility model is illustrated in further detail by embodiment, but the utility model not only limits
In these embodiments.
Used reagent is as follows in the examples below：
Silica gel, 200~300 mesh, Qingdao Bang Kai separation materials Co., Ltd；Phenyl trichlorosilane analyzes pure, Shanghai Mike
Woods biochemical technology Co., Ltd；Pyridine, toluene analyze pure, Sinopharm Chemical Reagent Co., Ltd.；Phosphoric acid analyzes pure, silver
Beneficial friend's chemical reagent Co., Ltd；Acetic acid analyzes pure, two factory of Tianjin chemical reagent；Methanol analyzes pure, Shandong Yu Wang groups；Mongolian oak
Pi Su (QUE), cyanidenon (LUT), Isorhamnetin (IRA) and Kaempferol (KAE) (analyzing pure, the resistance to Jilin Chemical of Town in Shanghai).
Solid-phase extracting instrument, standing grain industry science skill, China；High performance liquid chromatograph, Agilent 1100, the U.S.；Scanning electron microscope, JSM-
6701F, Japan；Specific surface area/Porosimetry, ASAP2010, the U.S.；Elemental analyser, Hanau, Germany；Infrared spectrum
Instrument, Nexus 870, the U.S..
1 phenyl bonded silica solid-phase extraction column of embodiment
The phenyl bonded silica solid-phase extraction column of the utility model is illustrated in the present embodiment.
As shown in Figure 1, the phenyl bonded silica solid-phase extraction column of the present embodiment has cylindrical glass cavity column tube 1,
Volume is 6mL, internal diameter 1.3cm；The cavity column tube 1 is being internally provided in thick 1mm, diameter and the cavity column tube 1
The consistent upper sieve plate 2 of diameter and lower sieve plate 4, the upper sieve plate 2 and the lower sieve plate 4 have sieve pore, and the aperture of the sieve pore is 5
μm；Filler 3 is filled between the upper sieve plate 2 and lower sieve plate 4, the filler is phenyl bonded silica.
In the present embodiment, the grain size of the filler 3 is 50~80 μm, usage amount 100mg；The ratio table of the filler 3
Area is 320m2/g。
The preparation of 2 phenyl bonded silica of embodiment
In the present embodiment, the preparation of phenyl bonded silica is carried out by following steps：It weighs 3.0g silica gel and is placed in 100mL first
In benzene, 1mL phenyl trichlorosilanes are added, adds 0.1mL pyridines as catalyst, above-mentioned system is stirred evenly, is heated back
12h is flowed, reaction is completed.Centrifugal treating product, ethyl alcohol, water wash repeatedly, and vacuum drying chamber drying obtains phenyl bonded silica.
Fig. 2 shows the scanning electron microscopic picture of phenyl bonded silica prepared by embodiment 2.It can be seen that phenyl bonded silica
The size of glue corresponds between 50~80 μm with the mesh number (200~300 mesh) of silica matrix.Simultaneously, it can be seen that benzene
The surface of base bonded silica gel is very coarse, and there are many small nano-size pores, illustrate that the specific surface area of phenyl bonded silica is larger.
Table 1 lists specific surface area, aperture and the elemental analysis result of phenyl bonded silica.It can be seen that phenyl bonding
The specific surface area of silica gel is up to 319.78m2/g.According to carbon content and specific surface area, every square metre of Silica Surface can be extrapolated
It has been bonded the phenyl of 4.12 μm of ol.In addition, the aperture of phenyl bonded silica and specific surface area are respectively less than silica matrix, reason exists
In the presence of phenyl occupies certain pore volume, and aperture and specific surface area is caused accordingly to reduce.
1 specific surface area of table/aperture and elemental analysis result
Fig. 3 shows the infrared spectrum of phenyl bonded silica and silica matrix, by comparing as can be seen that phenyl bonded silica
Glue is compared to silica matrix in the more absorption peaks of 699.12,739.27 and 1433.58 wave numbers.Wherein, 699.12,739.27 belong to
The C-H bond stretching vibration of phenyl, 1433.58 belong to the skeletal vibration of phenyl ring, which further demonstrates the successful key of phenyl
It closes on silica matrix surface.
The preparation of 3 phenyl bonded silica solid-phase extraction column of embodiment
It is in the present embodiment, described in embodiment 1 to be equipped in the cylindrical glass cavity column tube 1 of lower sieve plate 4,
The phenyl bonded silica prepared in the embodiment 1 of 100mg is fitted into as filler 3, then assembles upper sieve plate 2, compacting obtains phenyl
Bonded silica gel solid-phase extraction column.
The preparation of 4 flavones working solution of preparation example
By 4 kinds of Quercetin (QUE), cyanidenon (LUT), Isorhamnetin (IRA) and Kaempferol (KAE) flavones molecular mixings
It is dissolved in same methanol solvate, concentration is 0.1mg/mL, and adjusts pH value to 4.0, is stored in refrigerator as mother liquor, standby
With.Mother liquor is diluted to various concentration with distilled water, is used as working solution.
The Solid Phase Extraction of 5 chromocor compound of embodiment
In the present embodiment, first, 5mL methanol and 5mL water is used to extract phenyl bonded silica solid phase prepared by embodiment 3 respectively
It takes column to be eluted, activated, and empties peristaltic pump；Then, the flavones prepared in the preparation example 4 of 50mL is driven to work with peristaltic pump
Liquid makes flavones Molecular Adsorption in Solid Phase Extraction material surface by phenyl bonded silica solid-phase extraction column, flow velocity 2.0mL/min；
Then, it is eluted with peristaltic pump driving 1mL methanol, flow velocity 0.4mL/min obtains eluent.
In the above-described embodiments, applicant also carries out the pH value of the operating parameter of Solid Phase Extraction and flavones working solution
It considers below：
(1) loading volume
In extraction process, loading volume is an important parameter.In general, loading volume is bigger, enrichment times are got over
Height, detection limit are also lower, but the operating time is also longer；Loading volume is smaller, and enrichment times are lower, detection limit is also higher,
But the operating time is also shorter.In the present embodiment, the concentration of flavones working solution is fixed as 50.0 μ g/L, investigated 20 successively,
50,100,150,200, under the conditions of 250mL loading volumes chromocor compound recovery of extraction.From in Fig. 4 A it can be found that on
Sample volume is between 20~150mL, and recovery of extraction is higher and variation is little, and more than 150mL, the rate of recovery reduces, which says
Bright maximum loading volume is 150mL.150mL is should be less than as the final loading volume selected in extraction experiments, to ensure height
The rate of recovery.In addition, in terms of the selection of loading volume, enrichment times and operating time should be also taken into account.For example selection 100mL makees
It is higher then enrichment times are exactly 100 (elution volume is assumed to 1mL) for loading volume, but the operating time will extend to
100min (elution speed is assumed to 1mL/min) more takes.Consider enrichment times and operating time, final choice
50mL is as final loading volume.
(2) flavones working liquid ph
As a kind of natural polyphenol substance, the existence form of flavones molecule in aqueous solution is affected by pH value,
Also therefore, the pH value of working solution affects the recovery of extraction of flavones molecule.Fig. 4 B show flavones point under different pH condition
The recovery of extraction of son.It can be seen from the figure that at pH value 4.0, flavones molecule rate of recovery highest, this is because in the pH value
Under the conditions of, flavones molecule mainly exists with molecular forms in aqueous solution, and solubility is relatively low, can be easier to be adsorbed on phenyl key
Silica Surface is closed, so the rate of recovery is high；It is more than at 4.0 in pH value, the rate of recovery reduces, and reason is flavones molecule in aqueous solution
In mainly exist in the form of an ion, solubility is larger, it is difficult to be effectively adsorbed on phenyl bonded silica surface, so the rate of recovery drop
It is low；It is less than at 4.0 in pH value, the rate of recovery of flavones molecule is relatively low, and reason is that excessive acid molecule can occupy phenyl key
The adsorption site for closing Silica Surface, causes flavones Molecular Adsorption amount to decline, and all rate of recovery are relatively low.It is considered through complex optimum,
Applicant selects 4.0 pH value as loading working solution.
(3) loading speed
Fig. 4 C show influence of the loading speed to flavones recovery of extraction.As can be seen that loading speed is in 2.0mL/min
Within, the recovery of extraction of flavones molecule is higher and variation is little；Loading speed is higher than 2.0mL/min, and the rate of recovery reduces, this is
Due to loading excessive velocities, flavones molecule is caused not have sufficient chance to interact with phenyl bonded silica, it cannot be effective
Absorption, therefore the rate of recovery reduces.Balance through comprehensive consideration time cost and the rate of recovery, preferably loading speed are 2.0mL/min.
Further, applicant has also carried out following research to the parameter of elution step：
(4) selection of eluant, eluent
It in extraction experiments, needs to select eluant, eluent appropriate, to ensure that flavones molecule can be from phenyl bonded silica table
Face adequately elutes.Applicant has investigated methanol, ethyl alcohol, acetone, acetonitrile and the methanol solution containing 1.0% acetic acid and has been used as and washes
Recovery of extraction when de- agent, is as a result shown in Fig. 5 A.
According to Fig. 5 A as it can be seen that methanol and the methanol solution [w (acetic acid)=1.0%] containing acetic acid are used as eluant, eluent, flavones
Recovery of extraction highest and difference is little, and remaining organic solvent is difficult to effectively elute flavones molecule.From eluant, eluent cost, behaviour
Make complexity and recovery of extraction etc. to consider, it is preferable to use eluant, eluent of the methanol as chromocor compound.
(5) elution volume
When being eluted with methanol, elution volume is small as far as possible, to improve enrichment times, meanwhile, also save solvent
Consumption；On the other hand, elution volume should be enough to ensure that flavones molecule is fully eluted.
Fig. 5 B show the recovery of extraction of the flavones molecule under different methanol volumes.As can be seen that when elution volume is high
When 1.0mL, the rate of recovery is higher and variation is little, but when less than 1.0mL, the rate of recovery is then significantly lower.Therefore, it selects
1.0mL is as preferred elution volume.
(6) elution speed
Elution speed is also an important elution parameters.When speed is smaller, although the consuming time is longer, elution
Agent can adequately contact flavones molecule, so as to which effectively flavones molecule is eluted from phenyl bonded silica surface,
The rate of recovery is higher；And when excessive velocities, eluant, eluent is difficult to adequately contact flavones molecule, so, it is also difficult to it effectively will be yellow
Ketone molecule is eluted from fiber material surface, and the rate of recovery is relatively low.
Fig. 5 C show under different elution speeds, the recovery of extraction of flavones molecule.As can be seen that when elution speed exists
Within 0.4mL/min, recovery of extraction is higher, when more than 0.4mL/min, the rate of recovery is begun to decline.Therefore, consider the time
Cost and elution efficiency, preferably elution speed are 0.4mL/min.
The detection of 6 chromocor compound of embodiment
In the present embodiment, the chromocor compound in the eluent obtained to embodiment 5 using high performance liquid chromatography is carried out
Detection, testing conditions use following chromatographic condition：
ODS analytical columns (150mm × 4.6mm I.D.)；With methanol and H3PO4Aqueous solution [0.2wt%] is mobile phase A and B
Carry out gradient elution：0-0.5min is0.51-12.5min is12.51-25min isFlow rate of mobile phase：1.0mL/min；Column temperature：25℃；Sampling volume：20μL；UV detector, wavelength 360nm.
In the present embodiment, applicant further evaluates the result of aforementioned Solid Phase Extraction analysis.
The flavones molecular efforts liquid of the serial various concentration of configuration, under the conditions of aforementioned preferred extraction parameters, with this practicality
Novel phenyl bonded silica extraction column extracts the chromocor compound in above-mentioned working solution, and passes through high performance liquid chromatography
It is detected, then testing result is evaluated, results are shown in Table 2.
From the results shown in Table 2, the analysis method of the phenyl bonded silica base extracting flavone compound of the utility model
With the wide range of linearity, between 1~200 μ g/L, and linear relationship is good, linearly dependent coefficient (R) 0.9991~
Between 0.9999；The detection limit of flavones molecule is relatively low, is 0.25 μ g/L.The repeatability of single extraction pillar is good, opposite to mark
For quasi- deviation between 7.2%~9.4%, the reproducibility extracted between pillar is also preferable, relative standard deviation 8.4%~
Between 10.3%.The above results illustrate that the phenyl bonded silica solid phase extraction method established is suitable for the richness of chromocor compound
Collection and detection.
The evaluation of 2 phenyl bonded silica extracting flavone compound of table
The analysis of 7 actual sample of embodiment
In the present embodiment, using the method for embodiment 6 to red grape juice and honey jasmine tea (from local supermarket) two
Chromocor compound in kind actual sample is tested and analyzed, and testing result is shown in Table 3.
From the results shown in Table 3, Quercetin 19.9mg/L and Isorhamnetin are detected in red grape juice
13.1mg/L does not detect chromocor compound in honey jasmine tea.Further to confirm the reliability of the experimental method, toward two
4 kinds of flavones model compounds that 20 μ g/L are added in kind beverage, calculate recovery of standard addition.The result shows that 4 kinds of chromocor compounds
Recovery of standard addition between 89.2-92.4%, it was confirmed that the flavones in phenyl bonded silica extractive analysis actual sample
It is effective, reliable to close object.
The detection of chromocor compound and recovery of standard addition in 3 actual sample of table
ND=is not detected
Industrial applicibility
Compared with prior art, the utility model provides a kind of new phenyl bonded silica solid-phase extraction column, has
Prepare advantage simple and easy to do, of low cost, and can be simple and efficient by the phenyl bonded silica solid-phase extraction column pair
Chromocor compound is extracted, and then can be used for chromatography detection.This method has the wide range of linearity, low detection limit,
It is applicable to the enrichment detection of chromocor compound in a variety of actual samples, therefore before having good performance and wide application
Scape.
Claims (6)
1. a kind of phenyl bonded silica solid-phase extraction column, with glass cavity column tube (1), the glass cavity column tube (1) exists
It is internally provided with upper sieve plate (2) and lower sieve plate (4), filler (3), institute are filled between the upper sieve plate (2) and lower sieve plate (4)
It is phenyl bonded silica to state filler, and the grain size of the filler (3) is 50~80 μm, and usage amount is 80~120mg；The filler
(3) specific surface area is ＞ 300m2/g。
2. phenyl bonded silica solid-phase extraction column as described in claim 1, which is characterized in that the usage amount of the filler (3)
For 100mg.
3. phenyl bonded silica solid-phase extraction column as claimed in claim 1 or 2, which is characterized in that the glass cavity column tube
(1) shape is cylinder, volume 6mL；The internal diameter of the glass cavity column tube (1) is 1-1.5cm.
4. phenyl bonded silica solid-phase extraction column as claimed in claim 3, which is characterized in that the glass cavity column tube (1)
Internal diameter be 1.3cm.
5. phenyl bonded silica solid-phase extraction column as claimed in claim 3, which is characterized in that the upper sieve plate (2) and described
The diameter of lower sieve plate (4) is consistent with the internal diameter of glass cavity column tube (1)；The upper sieve plate (2) and the lower sieve plate (4)
With sieve pore, the aperture of the sieve pore is 3-10 μm；And/or the thickness of the upper sieve plate (2) and the lower sieve plate (4) be 1~
2mm。
6. phenyl bonded silica solid-phase extraction column as claimed in claim 5, which is characterized in that the aperture of the sieve pore is 5 μm.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201721169114.4U CN207913283U (en) | 2017-09-13 | 2017-09-13 | Phenyl bonded silica solid-phase extraction column |
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| Application Number | Priority Date | Filing Date | Title |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107441770A (en) * | 2017-09-13 | 2017-12-08 | 江易扬 | The extracting process and phenyl bonded silica solid-phase extraction column of chromocor compound |
| CN110508030A (en) * | 2019-09-18 | 2019-11-29 | 深圳市易瑞生物技术股份有限公司 | A kind of Magnetic solid phases extraction column and its application method |
-
2017
- 2017-09-13 CN CN201721169114.4U patent/CN207913283U/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107441770A (en) * | 2017-09-13 | 2017-12-08 | 江易扬 | The extracting process and phenyl bonded silica solid-phase extraction column of chromocor compound |
| CN110508030A (en) * | 2019-09-18 | 2019-11-29 | 深圳市易瑞生物技术股份有限公司 | A kind of Magnetic solid phases extraction column and its application method |
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